The Last Ship: The São Paulo Voyage of 1685

On the morning of 3 July 1685, the lookouts on the hills above Nagasaki saw something that, strictly speaking, should not have existed. A Portuguese frigate was standing into the harbour.

Forty-six years had passed since the shogunate had issued the final sakoku edict, expelling the Portuguese from Japan on pain of death. Forty-five years had passed since sixty-one Portuguese delegates from Macao had been beheaded at Nishizaka for making the mistake of testing that edict's sincerity. Thirty-eight years had passed since João IV's royal galleons had swung at anchor in this same bay for two months before being waved away without even the courtesy of an audience. The book on Portuguese–Japanese relations had not merely been closed. It had been burned, the ashes scattered, and a stone rolled over the spot.

And yet here, on a bright July morning in the second year of the Jōkyō era, was a small Portuguese ship flying its colours and asking politely if it might have a word.

The São Paulo of 1685 was the last Portuguese vessel ever to visit Japan. It was also the strangest. Unlike every Macanese delegation that had preceded it, it carried no silk and no silver. Unlike the doomed embassy of 1640, it carried no ambassadors in ceremonial silks. Unlike the royal galleons of 1647, it carried no letters from a king. What it carried was twelve or thirteen shipwrecked Japanese fishermen from the province of Isé, a calculated gamble dressed up as an act of charity, and a century's worth of Macanese longing for a trade that had never been replaced.

This is the story of how that final voyage went — and how the Tokugawa shogunate, for once in its long dealings with the Portuguese, chose to decline an offer without killing anyone.

The City That Would Not Let Go

Macao's Depression After 1639 and Its Canton Recovery in the 1680s

To understand why the São Paulo sailed at all, you have to understand the city that sent her — and the peculiar grief of a port that had lost its reason for existing.

Macao had been, for nearly a century, the single most profitable outpost of the Portuguese empire east of the Cape. The Nau do Trato — the Great Ship from Amacon — had for decades carried Chinese raw silk to Nagasaki and returned laden with Japanese silver at margins that sometimes exceeded 100 per cent. In 1637, in what would turn out to be one of the trade's final years, the silver carried out of Nagasaki by the Portuguese was valued at over 6.6 million florins — a figure comparable to the entire original capital of the Dutch East India Company. This was not trade. This was alchemy dressed up as shipping.

And then, in 1639, it ended.

The final sakoku edict slammed the door. The massacre of the 1640 embassy bolted it. The failure of the 1644–1647 royal embassy confirmed that the bolt was not going to be undrawn. In the history of Macao as in the ledgers of its Senado, the 1640s were catastrophic. The city's entire economic model had been predicated on a single sea route to a single port. That port was now closed with extreme prejudice. Its loss plunged Macao into a depression from which the city, in truth, never fully recovered.

The decades that followed were a slow, painful adjustment. Macao survived by diversifying — Manila, Makassar, Timor, Cochin-China, Siam, Tonkin — but none of these routes came close to the scale of what had been lost. The Dutch took Malacca in 1641, throttling a second vital artery. The violent Ming–Qing transition of the 1640s and 1650s disrupted Chinese supply chains and sent waves of refugees through the Pearl River delta. By the 1660s, the city's once-mighty merchant fleet had shrunk to perhaps ten or twelve relatively small vessels. Houses stood empty. Warehouses echoed.

Then, in the early 1680s, came the first real reprieve in forty years.

In 1680, the new Qing regime formally authorised Macao's trade, legitimising its commercial operations after decades of Ming–Qing uncertainty. In 1682, Macao secured a monopoly on the re-opened foreign trade at Canton for an annual fee of £8,000 — a sum the city could just about afford, in exchange for a revenue stream it could not afford to live without. Ships from Batavia, Manila, and the Coromandel Coast now had to pass through Macanese hands to reach the Chinese market. The city was breathing again.

And it was precisely in this moment of tentative recovery — when Macao had regained just enough confidence to think strategically — that a typhoon off the coast of Kyūshū blew a Japanese junk across the South China Sea and into the waters of the Pearl River.

Thirteen Men and an Idea

The Japanese Castaways of Isé and the Macao Senate's 1685 Plan

The Japanese vessel belonged to the coastwise trade of Isé, the coastal province southeast of Kyoto, and it should never have come anywhere near Macao. Japanese shipping was, by design of the shogunate, a home-waters affair. The ocean-going red-seal ships of the early Tokugawa period had been banned for half a century. Japanese merchants traded within sight of the archipelago or not at all. A junk from Isé, caught in a typhoon that bullied it fifteen hundred miles off course, was less a trading vessel than a corked bottle washed up on a foreign beach.

The twelve or thirteen men aboard — sources differ on the exact number — were fished out of the water by Macanese vessels and brought into the city. What happened next tells you everything about how Macao thought.

In any ordinary port, the castaways would have been handed over to the appropriate authorities, fed and housed, and eventually repatriated on whatever vessel happened to be making for their homeland. In Macao in 1685, they became, within days of their arrival, the centrepiece of a diplomatic plan.

The Senado da Câmara — the Leal Senado, Macao's famously fractious municipal council — convened to consider the windfall. The reasoning, set out in the deliberations preserved in the Arquivos de Macau, was straightforward almost to the point of naivety. Japan had expelled Portuguese merchants, priests, and ambassadors. Japan had never explicitly expelled the return of Japanese subjects by Portuguese hands. The edict of 1639 and the subsequent reinforcements of the sakoku policy had been, at every turn, about what the Portuguese brought into Japan. They had never been about what the Portuguese might quietly bring home.

Here, then, was an opportunity of surpassing elegance. A pretext so blameless, so humanitarian, so transparently lacking in any ulterior motive, that even the Tokugawa — famously the most suspicious government on earth — might be disarmed. Return the castaways. Ask nothing. Carry nothing. Say nothing. Let the gesture speak for itself. And if, in the afterglow of a courteous reception, the question of commerce could be raised — well, that was a matter for later.

The Senado took the castaways under official protection and voted to charter a ship.

What they were proposing was the kind of diplomatic manoeuvre that works beautifully on paper and terrifies everyone who has to execute it. To the older men around the council table, the logic was almost mathematically perfect. To anyone who remembered what had happened to the embassy of 1640 — and there were still men alive in Macao who did — the logic was a polite cover over a straightforward question: how many Macanese lives was the Japan trade worth this time?

The answer, encouragingly, turned out to be none.

A Ship in Ballast

What the São Paulo Carried to Nagasaki in 1685, and What She Did Not

The vessel chartered for the voyage was the São Paulo, a frigate of which almost nothing is known. The surviving sources — the Arquivos de Macau, Engelbert Kaempfer's History of Japan, the scattered references in the Boxer scholarship — do not record the name of her captain. They do not describe her tonnage with any precision. They do not note whether she was Macanese-built, Goa-built, or prize-taken. She is, historiographically, the faintest of the Nanban ships, a footnote sailing across footnotes.

What the sources do record, in unusual detail, is what she carried. And, more importantly, what she did not.

The Senado had thought hard about the catastrophe of 1640, and harder still about the rebuff of 1647. In each of those cases, the shogunate's objections had circled around what was aboard: silver, petitioners, priests, royal letters, commercial intentions. The São Paulo would carry none of these. She would sail in ballast — commercial ships' shorthand for a voyage carrying no cargo, only weight in the hold to keep the vessel stable. There were no bolts of silk, no chests of pepper, no bales of cotton, no trade goods of any description. There were no Jesuits. There were no friars of any order. There was no religious paraphernalia beyond what the crew required for their private devotions, and even this was carefully restricted. There were no letters from kings, no petitions, no memoranda, no ambassadors in gala dress. There was, in the stark phrasing of the Senado's resolution, nothing.

Nothing except the castaways, provisions for their journey, and a crew whose standing instructions were to behave with the absolute maximum of deference and the absolute minimum of initiative.

The São Paulo left Macao on 1 June 1685. The crossing was uneventful. After roughly a month at sea, on 3 July, she raised the hills of Kyūshū and stood into Nagasaki Bay.

What happened over the next two months is, in its strange way, one of the quietest encounters in the entire Nanban period — and one of the most revealing.

The Interpreters Who Still Remembered

Why Nagasaki Officials Still Spoke Portuguese in 1685

The first surprise came within hours of the frigate's anchoring.

A party of Japanese officials put out from Nagasaki to inspect the intruder. Among them were interpreters. And those interpreters, to the astonishment of the Portuguese crew, addressed them in Portuguese.

Forty-six years had passed since the final Portuguese vessels had sailed out of Nagasaki harbour. Forty-six years in which no Portuguese ship had legally entered a Japanese port. And yet here, in 1685, were officials of Nagasaki who could read, write, and speak the language fluently.

The reason was that the shogunate — in its characteristically contradictory fashion — had maintained a carefully curated pool of Portuguese-speakers at Nagasaki long after the Portuguese themselves were gone. The official interpreters' guild, the tsūji, was a hereditary institution. Families that had learned Portuguese in the first half of the seventeenth century, for the purposes of the Nagasaki trade, had passed the language on to their sons and grandsons — the state required its availability against the contingency of exactly this kind of moment. A Portuguese ship might yet come. A Kirishitan text might yet be discovered. A castaway might yet wash ashore. And when that happened, the shogunate wanted its own men on the boarding party, not Dutchmen hired from Deshima. There is something quite moving about this: a language kept alive in a single port by a small guild of men, preserved as a state asset for a future that, for most of those decades, would never come.

And then, in 1685, it did.

The Portuguese crew answered the interpreters' questions carefully. They had come, they said, to return the Japanese sailors rescued near Macao. They had come with no commercial purpose. They had brought nothing aboard that was forbidden by Japanese law. They requested, with all humility, to inform the authorities and — if it were possible — to be granted the favour of an audience regarding the traditional relationship between Japan and the Portuguese crown.

The officials recorded the answers. They recorded, separately, the testimonies of the Japanese castaways themselves. The two accounts, it turned out, matched in every particular.

The following day, the inspection began in earnest.

The Inspection

How Nagasaki Searched the São Paulo and Held Her Crew

The Japanese authorities, having learned from 1640 and 1647 that Portuguese ships could not always be taken at their word, conducted the kind of search that left nothing to luck. Every chest was opened. Every locker was emptied. Every crewman's sea-bag was turned inside out. Every compartment below decks was scrutinised by officials looking specifically for contraband of two categories: commercial goods of any kind, and religious articles of any description. Crosses, rosaries, holy pictures, medals, printed prayers, sacred vessels — anything that might suggest a covert missionary purpose was what the inspectors most feared finding, and what they most thoroughly hunted.

They found nothing.

The Portuguese, it turned out, had been telling the truth. The ship was empty.

Having satisfied themselves on this point, the Japanese authorities moved to the second phase of the procedure. The castaways were permitted to disembark and were placed in Japanese custody. The Portuguese crew was not permitted to disembark. The ship's rudder was removed. The sails were struck and taken ashore. The arms and ammunition were confiscated. All of this, the officials carefully explained, was standard procedure; everything would be returned when the vessel was granted permission to leave.

What is striking about this whole sequence — and what distinguishes it so sharply from the savage protocols of 1640 — is the tone. The Japanese were not hostile. They were scrupulous. The governor of Nagasaki, a figure who in the earlier catastrophes would have been readying executioners, instead arranged for the Portuguese to be kept under guard in the harbour and well supplied with fresh water, rice, fruit, fish, and vegetables while they waited for word from Edo. It was as if, having satisfied themselves that the São Paulo was exactly what it claimed to be, the Japanese had decided to treat her crew not as criminals but as unexpected and slightly awkward guests.

Which, in a very real sense, is what they were.

The dispatches went to Edo. In the Tokugawa system, nothing of this magnitude could be decided locally. The governor of Nagasaki was a formidable official, but he was not about to improvise a response to the first Portuguese vessel to enter Japanese waters in nearly half a century. The matter would be decided by the rōjū — the senior council — and ultimately by the shogun himself. In 1685, that shogun was Tokugawa Tsunayoshi, son of Iemitsu, fifth of the Tokugawa line. He was not known for his leniency, and he was famously fond of the kinds of elaborate rituals and punctilious procedures that made Tokugawa governance feel, to its subjects, at once inescapable and deeply inscrutable.

The Portuguese crew waited.

They waited, as it turned out, for over a month.

The Shogun's Answer

Tokugawa Tsunayoshi's Reply of 6 August 1685

On 6 August 1685, the response from Edo arrived. It was, in its way, a minor masterpiece of Tokugawa statecraft.

The reply, delivered formally to the Portuguese through the interpreters, was composed of two elements carefully calibrated to coexist.

The first was gratitude. The shogun wished it to be known that the authorities of Japan were thankful for the kindness and trouble the Portuguese had taken in rescuing the castaways of Isé and returning them to their homeland. As a token of this gratitude, and to ensure that the crew of the São Paulo did not suffer want on their return voyage, the shogun had ordered that the ship be provisioned with thirty sacks of rice, abundant fresh food, water, and all necessary supplies for the journey home. The Portuguese were to accept these provisions as a gift from the Japanese government.

The second was the prohibition. In language of exquisite courtesy and utter finality, the shogun instructed the Portuguese to inform the governor of Macao that ships from Macao were never again to come to Japan, under any pretext whatsoever. The sakoku edicts remained in force. The prohibition on Christian propagation remained in force. The ban on Portuguese entry remained in force. The return of shipwrecked Japanese subjects was appreciated, but it could not — and would not — serve as the basis for a resumption of relations of any kind. If, at some future date, another Portuguese vessel were to enter Japanese waters for any reason, the consequences would be those prescribed by the edict of 1639.

The framing is worth pausing over.

There is, in the shogun's reply, none of the rhetorical violence of the 1640 sentence, when the Portuguese ambassadors had been called "villains" and read a death warrant in their gala dress. There is none of the wordless stonewalling of 1647, when Siqueira de Souza's galleons had been ignored into departure. There is, instead, something that reads almost like a courtly letter of regret. The Portuguese had done a good thing. The Portuguese would be rewarded for doing it. But the Portuguese were not to interpret the reward as an opening. The door, the shogun was saying in the most polite terms available to a Tokugawa chancery, remained closed — and the politeness itself was the proof of how comprehensively closed it was.

The victory, in other words, had become so complete that it could now be dressed in kindness.

Departure

When the São Paulo Left Nagasaki: 30 August or 23 September 1685

The return of the rudder, the sails, the arms, and the ammunition proceeded in the reverse of the sequence by which they had been taken. The governor of Nagasaki, in a final courtesy, asked the Portuguese captain to shift the São Paulo to an anchorage some distance from the harbour entrance before departure — a last discreet reminder that the ship's presence in the inner harbour was a concession, not a right — and inquired politely when the vessel intended to sail.

The São Paulo was delayed for some weeks by unfavourable winds. The sources give slightly different dates for her eventual departure: some place it on 23 September 1685, others as early as 30 August. The discrepancy is less significant than it looks; both reflect a vessel that, having received its answer, took the next available weather window and made for home. The passage back to Macao was uneventful. The ship arrived in the autumn, delivered the news to the Senado, and slipped back into the obscurity of the Macanese archives from which her name had briefly emerged.

The castaways, one assumes, returned to Isé.

The Portuguese, one knows for certain, never came back.

The German Chronicler

Engelbert Kaempfer's Account of the São Paulo Voyage

Five years after the São Paulo sailed home, a German physician in the service of the Dutch East India Company stepped onto the narrow fan-shaped island of Deshima and began what would become the most sophisticated European study of Tokugawa Japan ever written.

Engelbert Kaempfer arrived in Nagasaki Bay on 23 September 1690 and resided at the Dutch factory until 1692. In his two years there, he interviewed interpreters, questioned Japanese officials, combed the records of the Dutch trading post, and compiled notes that would eventually be published posthumously in 1727 as The History of Japan. Among the many things Kaempfer recorded was a concise and, by the standards of the available evidence, reasonably accurate account of the São Paulo voyage of five years earlier.

The Dutch had watched the São Paulo's arrival with the sharpest possible professional interest. Every Portuguese vessel that appeared in Nagasaki was, from the Dutch point of view, a potential threat to the exclusive trading position they had inherited at such great cost.

Between the two archives, Macao and Deshima, East and West, Catholic and Protestant, the story survives. The São Paulo's single round trip generated more surviving documentation than many of the merchant voyages of the preceding century.

History is kind like that sometimes: the smallest ships leave the deepest wakes.

A Quiet End to a Noisy Relationship

How the Nanban Period Ended: 1543 to 1685

The Nanban period began, by convention, in 1543, with three Portuguese adventurers stepping ashore on a beach at Tanegashima and discovering — somewhat to their own surprise — that they had arrived in Japan. It ended, depending on which ending you prefer, in 1639 with the sakoku edict, in 1640 with the Nishizaka beheadings, in 1647 with the departure of João IV's galleons, or — in its truest and most formal sense — in 1685, with a small frigate dropping its Nagasaki anchorage and sailing home to Macao with thirty sacks of rice.

The symmetry is almost too neat. The relationship opened with an accident — a Chinese junk blown off course by a typhoon, carrying the first three Portuguese by sheer weather to the first Japanese port to receive them. It closed with the mirror image: a Japanese junk blown off course by a typhoon, carrying the last Japanese to be delivered to Nagasaki by Portuguese hands. Between those two accidents lay 142 years of silk and silver and faith and fire. Tanegashima firearms. The mission of Francis Xavier. The great golden screens. The Tenshō Embassy. The 26 Martyrs. The San Felipe Incident. The Madre de Deus affair. The Shimabara Rebellion. Thousands of lives taken. Hundreds of thousands of converts made. Castles won, cities founded, languages traded, foods invented, fortunes made and lost and made again. And then — at the very end — a short, polite letter from a shogun, thirty sacks of rice, a fair wind for home.

What the São Paulo voyage demonstrated, more than anything, was that the Tokugawa had won so thoroughly that they could afford to be gentle. In 1640, the shogunate had killed sixty-one men because the prohibition was still new, still untested, still in need of reinforcement through spectacle. In 1685, the prohibition was an old law on an old book, a fact of nature as settled as the tides of Nagasaki Bay. It required no further reinforcement. A courteous dismissal was sufficient because a courteous dismissal was the truth: the Japan of Tsunayoshi no longer needed the Portuguese, no longer feared them, and no longer required their blood to make a point that every literate person in East Asia already understood. The Dutch at Deshima, confined to their little fan of reclaimed land in Nagasaki harbour, would carry the whole of European commerce with Japan on their shoulders for the next 168 years, until Commodore Perry's squadron arrived in 1853 and made the next history.

For Macao, the news the São Paulo brought home was, in its way, a second bereavement. The first had been the shock of 1639 — the abrupt loss of a trade, a livelihood, a reason for being. The second was the quiet realisation of 1685 that the loss had become permanent by general consent of the universe. The Japan trade was not coming back. The hope that had sustained a generation of Macanese merchants — the hope that some combination of patience, diplomacy, castaways, and luck might one day reopen the door — was over. It was time, finally, to accept it and build a different city.

And Macao did. The city turned inward and outward at once, deepening its Canton monopoly, expanding its presence in Southeast Asia, and reinventing itself, over the following two centuries, as something different from what it had been: less a Nanban outpost, more a Sino-Portuguese entrepôt, a place whose identity was no longer anchored in a single lost trade but in a thousand smaller ones. The Pearl River would have its own history, and it would not be Japan's.

The São Paulo never sailed to Japan again. Neither did any other Portuguese vessel. The last direct contact between the kingdom that had introduced firearms to Tanegashima and the kingdom that had received them ended not with a massacre but with a bow, a gift of rice, and the polite, unambiguous word no — spoken through interpreters who still remembered how to say it in Portuguese.

It was the only ending the relationship ever really had a chance of receiving.

It came, as these things sometimes do, forty-six years too late to make any difference.

Sources & Further Reading

Boxer, Charles R. The Great Ship from Amacon: Annals of Macao and the Old Japan Trade, 1555–1640. Centro de Estudos Históricos Ultramarinos, Lisbon, 1959. The foundational English-language study of the Macao–Nagasaki trade and its aftermath.

Boxer, Charles R. The Christian Century in Japan, 1549–1650. University of California Press, 1951. Boxer's classic account of the Portuguese encounter with Japan, indispensable for the background against which the São Paulo voyage must be read.

Kaempfer, Engelbert. The History of Japan, Together with a Description of the Kingdom of Siam. Translated by J. G. Scheuchzer. 2 vols. London, 1727. The earliest detailed European account of the São Paulo voyage, compiled by a German physician resident at Deshima in 1690–92. Modern critical edition by Beatrice Bodart-Bailey, Kaempfer's Japan: Tokugawa Culture Observed (University of Hawaii Press, 1999).

Arquivos de Macau. Series I, II, and III. Governo de Macau / Leal Senado, 1929–1995. The official archives of the city of Macao, containing the Senate's deliberations, correspondence, and administrative records for the period, including the charter of the São Paulo and the Senate's account of her reception at Nagasaki.

Souza, George Bryan. The Survival of Empire: Portuguese Trade and Society in China and the South China Sea, 1630–1754. Cambridge University Press, 1986. The most thorough modern study of Macao's economic history in the century after the loss of the Japan trade, with extended treatment of the Canton monopoly of 1682 and the city's diversification into Southeast Asian networks.

Ptak, Roderich. China, the Portuguese, and the Nanyang: Oceans and Routes, Regions and Trade (c. 1000–1600). Ashgate, 2004. Context for Macao's position within the wider networks of East and Southeast Asian maritime commerce.

Laver, Michael S. The Sakoku Edicts and the Politics of Tokugawa Hegemony. Cambria Press, 2011. An essential reinterpretation of the sakoku system as a controlled engagement rather than total isolation, with close attention to how the Tokugawa managed foreign contact throughout the later seventeenth century.

Cooper, Michael. They Came to Japan: An Anthology of European Reports on Japan, 1543–1640. University of California Press, 1965. A carefully curated collection of primary European accounts of Japan, useful for establishing how the Portuguese saw the country they had been expelled from — and why Macao's merchants could not stop longing for it.

Massarella, Derek. A World Elsewhere: Europe's Encounter with Japan in the Sixteenth and Seventeenth Centuries. Yale University Press, 1990. A magisterial synthesis of all European engagements with Japan across the long Nanban century, essential for placing the São Paulo voyage in its full comparative context.

Jansen, Marius B. The Making of Modern Japan. Harvard University Press, 2000. The standard one-volume history of Japan, with useful context on the shogunate's handling of foreign contact during the reign of Tsunayoshi.

Nagazumi, Yōko. Kinsei shoki no gaikō [Diplomacy in the Early Modern Period]. Sōbunsha, 1990. Japanese-language treatment of Tokugawa foreign relations.

Boxer, Charles R. Fidalgos in the Far East, 1550–1770. Martinus Nijhoff, 1948; repr. Oxford University Press, 1968. Boxer's earlier study of Portuguese society in Macao, with vivid portraits of the Senado da Câmara and the merchant class who sent the São Paulo on her last mission.

Coates, Austin. A Macao Narrative. Heinemann Asia, 1978; repr. Hong Kong University Press, 2009. A readable general history of Macao, drawing extensively on the Arquivos for episodes such as the São Paulo voyage.

Wills, John E., Jr. Pepper, Guns, and Parleys: The Dutch East India Company and China, 1662–1681. Harvard University Press, 1974. Though centred on the Dutch, Wills's work provides crucial context for the Qing regulatory environment within which Macao secured its 1680s recovery — the necessary precondition for the São Paulo ever sailing at all.